Triphenylphosphine → 2-(2-Chlorophenyl)ethenylbenzoic acid

HRID 1722826Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23]Cl.[CH:29]1[CH:34]=[C:33]2[CH:35]([OH:39])[O:36][C:37](=O)[C:32]2=[CH:31][CH:30]=1.C[O-].[Na+]>CO>[Cl:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=[CH:37][C:32]1[CH:31]=[CH:30][CH:29]=[CH:34][C:33]=1[C:35]([OH:39])=[O:36]

Participants

Conditions

Temperature: 0 °C

Procedure

To 78 g (297 mmol) of triphenylphosphine in 150 ml of methanol were added dropwise with stirring 48.3 g (300 mmol) of 2-chlorobenzyl chloride, and the reaction mixture was heated under reflux for 2 hours. After the reaction mixture had been cooled down to 0° C., 46.4 g (309 mmol) of o-phthalaldehydic acid were added with stirring in the course of about 1 min. Thereafter 135 g (750 mmol) of a 30% strength solution of sodium methylate in methanol were added at 0°-10° C. with stirring in the course of 45 min and stirred in at 0°-10° C. for 3 hours, and the reaction mixture was worked up in a conventional manner to give 72 g (94%) of (E/Z)-2-[2-(2-chlorophenyl)ethenylbenzoic acid in a ratio of ~11:89 in the form of colorless crystals having a melting point of 144°-148° C.

Workup

temperaturethe reaction mixture was heated
temperatureunder reflux for 2 hours
stirringwith stirring in the course of 45 min
stirringstirred in at 0°-10° C. for 3 hours

Sources & evidence

ORD record: ord-1f5b93b4561f4c7aab6b23e8d46d015f
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04857658

Reaction notes

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